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It’s very difficult question to answer. How do you judge a leader? Is it financial success? The loyalty they engender? Their ability to inspire? There are war-time leaders and peace-time leaders. Leaders may be understated or zealous. I’m not sure we’ll ever be able to say definitively what constitutes a great leader. Regardless, we all want to improve our ability to lead, whether it’s a small team or a Fortune 500.

Over the weekend, the NY Times interviewed a classmate of mine from Dartmouth and fellow oarsman on the freshman crew team, Cal Newport, about his book and his idea, Deep Work. Here’s the crux of the idea:
Deep work is my term for the activity of focusing without distraction on a cognitively demanding task. It describes, in other words, when you’re really locked into doing something hard with your mind…In order for a session to count as deep work there must be zero distractions.

Your startup is growing quickly. To hit next year’s target, you may need to hire many people. Where do you start? Bottoms up or top down? Both are viable strategies, but hiring a strong management team at every level provides some key benefits. First, they help you hire more effectively. Second, they will guide new additions to the team to success. Third, they will reduce unnecessary turnover.
As you grow, your company well need to interview and hire large numbers of new people.

How much can a customer success manager manage? I’d heard the wisdom of $1-2M in ARR per year and around 80 accounts. But I hadn’t come across any data. Last summer, Gainsight posted the results of their survey on the topic. The truth is most CSMs manage between $2-5M in ARR and somewhere between 10-500 accounts. But it varies by segment.
The charts above display Gainsight’s data. I’ve reformatted them to compare segments side-by-side.

Last year, I talked wrote 1% of Salesforce’s Revenue Makes a Unicorn.The post talked about the potential in the SaaS ecosystem for startups to identify underserved customers in existing installed bases of incumbents and build big companies serving them better. Kustomer is a customer support software business based in New York that is doing just that. And today they’re announcing two milestones for the business: their $35M Series C and 5x annual growth.

In the car yesterday, I listened to an interview with Eugene Wei, who described the dynamics of consumer technology as if they were plain as day. It’s rare to hear someone lucidly describe complex topics like the reasons for Twitter’s success and struggles. Eugene wrote many of his ideas in this post though there are some ideas that I found only in the podcast.
Eugene was an early PM at Amazon, SVP of Product and Marketing at Hulu, Head of Product at Flipboard, and Head of Video at Oculus.

I’m thrilled to welcome Travis Bryant as an entrepreneur-in-residence (EIR) to Redpoint. I first heard Travis speak at a technology conference a few years ago. I noticed then that his thinking on go-to-market strategy is among the most modern in Startupland because it combines all of the key aspects of SaaS go-to-market in novel ways.
Travis started his career in technology as an Oracle database administrator but moved into sales. He became VP of Commercial Sales at Salesforce, then SVP Sales at Optimizely and helped them grow from single digits to tens of millions of ARR.

In 2015, I wrote about the trade-off facing vertical SaaS companies. Vertical SaaS companies focus their efforts on a particular group of customers. Procore targets construction with their software and Veeva targets pharmaceuticals with their CRM. This concentration limits the market size, but improves product market fit. Both of those businesses are now worth more than $3B. There is a new twist in SaaS with a parallel dynamic.
I’ve started to call them AI Agencies.

In their book,It Doesn’t Have to Be Crazy at Work, Jason Fried and David Heinemeier Hansson, the founders of 37Signals share how they’ve built and run their very successful company Basecamp. There’s a novel idea in the book: your company is a product used by its employees.
[W]hen you think of the company as a product, you ask different questions: Do people who work here know how to use the company?

In the public stock market, share repurchases/buybacks have reached more than $1 trillion in 2018, a historic high. As the amount of private capital increases, share repurchases in startups are popping up. Typically, they are a very inefficient use of capital.
A share repurchase occurs when the company uses cash on its balance sheet to buy shares from an existing shareholder, typically an employee or an early investor.
For public companies, buying shares is a way of using excess capital to increase the earnings per share (EPS) and other metrics that investors care about.